One night in August 2022, after a long day of showing at Galway Downs in Temecula, California, eventer Tommy Greengard and his coach Andrea Pfeiffer separately paused on the same Facebook picture. In it, a bright-eyed chestnut gelding stood before an English brick manor, his gaze fixed on the distance. Greengard went to bed with the gelding on his mind. The next morning, he learned the horse had also been on Pfeiffer’s.

“I sent a text to Tommy, and I said, ‘What do you think of this?’ ” Pfeiffer said of sending Greengard the horse’s photo. “And he was like, ‘Oh, my God, I saw it too. I was going to call you.’ I said, ‘Well, we already bought it.’ ”

Pfeiffer had already had a busy morning, calling her friend Matt Flynn, who’d only just acquired the sale horse from the photo named That’s Me Z. She asked a few questions about the Zangersheide (Take A Chance On Me Z—Veneita, VDL Indoctro) before she told Flynn, “Send me the X-rays; we’re ready to go.”

Knowing the horse from just his photo and then a few follow-up videos, they had little idea of his personality. The gelding that finally stepped off the plane in the U.S. was much more than a picture-perfect face; he was full of charisma and not a few quirks. “Z” was a stall walker, picky about his trusted people, and “worried by nature,” Greengard said.

“He’s a weirdo” Pfeiffer said with a laugh. “He is not for everybody; Z is weird. But we do weird well.”

Even with his emerging eccentricities, there were no regrets about buying the horse off a photo and a gut feeling.

“He captured both of our imaginations from Day 1,” Greengard said.

At their eventing program Chocolate Horse Farm in Petaluma, California, the coach and rider began getting to know the green gelding. Greengard remembers their first competition as symbolic of Z’s nervous early days with the team.

“At his first show in California, he spent the entire day in a halter with Andrea coaching,” Greengard said. “So it was Andrea on her golf cart coaching 30 people at Woodside Horse Park—literally 30. It was Andrea, her golf cart, a hay net, and Z in a halter. That pretty much sums up the relationship.”

But the spark that made Z “weird” also made him remarkable. Within a few weeks of arriving in the U.S., he qualified for—and won—the USEA Young Event Horse West Coast 5-Year-Old Championship, posting the highest score in the country. The horse who captured their imaginations was now realizing his potential, and that bit of success had the trainers dreaming of more possibilities.

“In the coming days, we hatched that sort of long-range plan that maybe this could be a 7-year-old that’s good enough to go to [Le] Lion,” Pfeiffer said. “So we just had kind of a little slow burn for two years, just plodding along, just carefully curating a program to see if we could get there.

“We did believe in him,” she added. “But we were very cautious in the beginning not to go too far.”

In 2023, Greengard planned to take Z overseas, where they trained with Tim and Jonelle Price in England to prepare for the FEI WBFSH Eventing World Breeding Championships for Young Horses in Le Lion-d’Angers, France, to contest the CCI3*-L.

As plans for the trip took shape, Pfeiffer realized that there were more Chocolate Horse horses who would benefit from spending the season abroad. “We ended up from one horse to five in quick succession,” Pfeiffer said.

“We had an incredible group of horses,” she continued. “For four months, [Greengard] showed all across England. So by the time Z went to France, he was very well-versed, very settled. Tommy’s confidence was at an all-time high. What a success.”

They finished 16th in the CCI3*-L at Le Lion, and Greengard returned to California certain of how much their partnership had matured.

“You know, one of the things that I’m most proud about is we were very clear-headed on what that trip was about, and it was about education and learning more,” Greengard said. “I left on that trip, and I was like, ‘I don’t care how we do. I don’t care about any of the stats. I want to come home, and I want to have learned more, and I want to have happy, sound horses that are more educated.’ I feel like we did that in spades, and that has been a huge catalyst for our success this year.”

That catalyst propelled the pair to finish second in the CCI4*-S at Galway Downs in April and third in the CCI4*-S at The Event at Rebecca Farm (Montana) in July. The pair also earned 17th in the competitive Cosequin Lexington CCI4*-S, held alongside the Defender Kentucky Three-Day Event, in April.

“He’s very much always had a very good meter for where he was at in terms of what was an appropriate ask,” Greengard said. “I think we’ve seen that this year; he’s really stepped up to the advanced level with loads of confidence, and it’s gotten better every time out. That was the mark of making good decisions for the horse.”

At the USEA American Eventing Championships held in late August, Greengard felt they’d reached a milestone in Z’s confidence. The pair led the $60,000 Adequan Advanced Final for all three phases, finishing on a score of 44.8—more than 14 penalties ahead of second-placed Karen O’Neal on Clooney 14.

Every Stride, Every Horse

Greengard, 26, was ready for a horse like Z because of the work he’s been doing with Pfeiffer since 2020. He grew up in Malibu, California, riding with Robyn Fisher, and landed at Pfeiffer’s Chocolate Horse while studying sustainability at University of California, Berkeley. Pfeiffer says that when she first met the young rider, he was talented with a great foundation but was often a little too self-disciplined.

“When he arrived, he was young,” she said. “He was a good rider. He was really methodical. It was almost to the point he was so methodical, I’m like, ‘OK, it’s time to get off that 20-meter circle.’ And he goes, ‘Ah, did you see those two steps?’ And I’m like, ‘No, I think my eyes were closed, sleeping. Two steps isn’t going to do it. We’ve got to move on!’ ”

But Pfeiffer appreciated the level of care that Greengard put into every stride and every horse—and she could also see that he was exceptionally smart. She helped the young eventer learn to zoom out from the granular details and think big picture.

“Where he’s really gained the knowledge is in the creativity of riding,” Pfeiffer said of Greengard. “He came to me very correct. I said, ‘You always color inside the lines; the sky is blue, and the grass is green, and the sun is yellow.’ I said, ‘Now is the time we’re going to paint outside the lines, and we’re going to use colors that don’t make sense. You need to learn now to be an artist and not so regimented.’ ”

When Z came along, he was a horse that required a balance of both the granular—he thrived with a routine—and a creative approach. The pair carefully strategized a program that ensured he had lots of turn-out and time off. And when it came to competitions, they had one goal: to make Z feel good about himself.

“We’ve been super careful not to exploit his generosity,” Pfeiffer said. “You know, if anybody looks up Z’s record, he goes up a level, he drops back a level or two—not because it went wrong, because it went so well. So any time he’s done something big, he comes home, and then we’ll drop him down a level. We’ll let him do something easy. So the goal is that he always feels mighty every time he goes out, but every time he goes out, he’s not asked to do the hardest thing he’s ever seen.”

After their AEC win, Greengard said it was clear that they had met their goal, and he joked that Z was “beaming” the next morning.

And, true to their word, for Z’s next outing after the AEC, he dropped down to intermediate at the Aspen Farms Horse Trials and USEA Area VII Championships, held Sept. 12-14 in Yelm, Washington, where he finished second to Balladeer Kilbrickens Lad, who Greengard rode for owner Patricia Culleton. The back-and-forth keeps Z feeling confident in himself, and that confidence shows to the world around him.

“He’s not a big horse, but he walks incredibly tall,” Pfeiffer said. “He has this little funny swing to his head; he twirls it as he walks, and then he has the walk that the dressage judges hate where he really flings his feet. It just makes me laugh. We work really hard in the dressage ring for him not to do that. But I mean, he really will come out of his stall and strut around. He knows he owns the world.”

Even if the dressage judges frown on Z’s exaggerated, toe-flicking walk, Pfeiffer said she treasures this little flaw, knowing it’s Z’s way of saying that he feels good in his skin.

She’s happy to see that their program is making the young horse braver and braver.

“It’s all about keeping Z’s confidence so he feels like Superman,” she said. “He wears a cape, and away we go, you know? I mean, that horse really does: He wears a cape every day.”

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This article originally appeared in the September 2025 issue of The Chronicle of the Horse. You can subscribe and get online access to a digital version and then enjoy a year of The Chronicle of the Horse. If you’re just following COTH online, you’re missing so much great unique content. Each print issue of the Chronicle is full of in-depth competition news, fascinating features, probing looks at issues within the sports of hunter/jumper, eventing and dressage, and stunning photography.